US4410538A - N-Disubstituted aniline derivatives, their preparation, their use as microbicides and agents for such use - Google Patents

N-Disubstituted aniline derivatives, their preparation, their use as microbicides and agents for such use Download PDF

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US4410538A
US4410538A US06/287,684 US28768481A US4410538A US 4410538 A US4410538 A US 4410538A US 28768481 A US28768481 A US 28768481A US 4410538 A US4410538 A US 4410538A
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methyl
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Gerhard Hamprecht
Eberhard Ammermann
Ernst-Heinrich Pommer
Peter Plath
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BASF SE
Toyota Motor Corp
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Assigned to TOYOTA JIDOSHA KABUSHIKI KAISHA reassignment TOYOTA JIDOSHA KABUSHIKI KAISHA ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: KUBO, SEITOKU, KURAMOCHI, KOUJIRO, KYUSHIMA, TATSUO
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms

Definitions

  • the present invention relates to novel N-disubstituted aniline derivatives, processes for their preparation, microbicides which contain these compounds as active ingredients, and processes for control of fungi.
  • Heterocyclic carboxylic acid anilides which have a microbicidal action are disclosed in German Laid-Open Applications DOS No. 2,513,732 and DOS No. 2,513,788.
  • Heterocyclic radicals in these compounds are pyridyl, pyrimidinyl, dihydropyranyl, dihydro-1,4-oxathiinyl, thienyl and furyl. These compounds are insufficiently active against Phytophthora.
  • N-disubstituted aniline derivatives of the formula I ##STR2## where R is C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 2 -C 4 -alkoxyalkyl or halogen, R 1 is C 1 -C 4 -alkyl or halogen, R 2 is hydrogen, C 1 -C 4 -alkyl or halogen, R 3 is CH[OR 5 ] 2 , COOR 5 or COSR 5 , R 5 being C 1 -C 4 -alkyl, and R 4 is unsubstituted or methyl-, nitro- or halogen-substituted 1,2,3-thiadiazol-4-yl or 1,2,3-thiadiazol-5-yl, possess excellent microbicidal activity and are superior to known heterocyclic carboxylic acid anilides in their action, especially against Phytophthora.
  • Preferred microbicides are compounds of the formula I, where R, R 1 and R 2 independently of one another are methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec.-butyl, tert.-butyl, fluorine, chlorine, bromine or iodine, R can also be methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxy, ethoxy or n-propoxy, R 2 can also be hydrogen, R 3 can also be dimethoxymethyl, carbomethoxy or carbomethylmercapto and R 4 has the stated meanings.
  • Particularly preferred compound of the formula I are those where R is methyl, R 1 is methyl, ethyl or chlorine, R 2 is hydrogen or methyl, R 3 is dimethoxymethyl, carbomethoxy or carbomethylmercapto and R 4 is 1,2,3-thiadiazol-4-yl or 1,2,3-thiadiazol-5-yl.
  • the compounds of the formula I can be prepared by reacting a compound of the formula II ##STR3## where R, R 1 , R 2 and R 3 have the above meanings, with a carboxylic acid derivative of the formula III ##STR4## where R 4 has the above meanings and A is a nucleophilically displaceable leaving group.
  • A is, for example, halogen, eg. chlorine or bromine, alkoxycarbonyloxy, eg. methoxycarbonyloxy or ethoxycarbonyloxy, benzyloxycarbonyloxy or an azolyl radical, eg. imidazolyl or triazolyl.
  • halogen eg. chlorine or bromine
  • alkoxycarbonyloxy eg. methoxycarbonyloxy or ethoxycarbonyloxy
  • benzyloxycarbonyloxy eg. imidazolyl or triazolyl.
  • halohydrocarbons especially chlorohydrocarbons, eg. tetrachloroethylene, 1,1,2,2- and 1,1,1,2-tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, chloronaphthalene, dichloronaphthalene, carbon tetrachloride, 1,1,1- and 1,1,2-trichloroethane, trichloroethylene, pentachloroethane, o-, m- and p-difluorobenzene, 1,2-dichloroethane, 1,1-dichloroethane, 1,2-cis-dichloroethylene, chlorobenzene, fluorobenzene, bromobenzene, iodobenzene, o-, m-
  • ethyl propyl ether methyl tert.-butyl ether, n-butyl ethyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, diisopropyl ether, anisole, phenetole, cyclohexyl methyl ether, diethyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, thioanisole and ⁇ , ⁇ '-dichlorodiethyl ether; nitrohydrocarbons, eg.
  • heptane pinane, nonane, o-, m- and p-cymene, gasoline fractions boiling within a range of from 70° to 190° C., cyclohexane, methylcyclohexane, decalin, petroleum ether, hexane, naphtha, 2,2,4-trimethylpentane, 2,2,3-trimethylpentane, 2,3,3-trimethylpentane and octane; esters, eg. ethyl acetate, ethyl acetoacetate and isobutyl acetate; amides, eg. formamide, methylformamide and dimethylformamide; ketones, eg.
  • the amount of solvent used is from 100 to 2,000% by weight, preferably from 200 to 700% by weight, based on starting material II.
  • suitable basic compounds are potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, lithium hydroxide, lithium carbonate, sodium bicarbonate, potassium bicarbonate, calcium hydroxide, calcium oxide, barium oxide, magnesium hydroxide, magnesium oxide, barium hydroxide, calcium carbonate, magnesium carbonate, magnesium acetate, zinc hydroxide, zinc oxide, zinc carbonate, zinc acetate, sodium formate, sodium acetate, trimethylamine, triethylamine, tripropylamine, triisopropylamine, tributylamine, triisobutylamine, tri-sec.-butylamine, tri-tert.-butylamine, tribenzylamine, tricyclohexylamine, triamylamine, trihexylamine, N,N-dimethylaniline, N,N-diethylaniline, N,N-dipropylaniline, N,N-dimethyltoluidine, N,N-diethyltoluidine
  • the hydrogen halide formed in the reaction can also be removed by passing an inert gas, for example nitrogen, into the mixture.
  • an inert gas for example nitrogen
  • the reaction can be carried out in the presence or absence of an accelerator.
  • Preferred accelerators include metal halides, eg. sodium bromide and potassium iodide, azoles, eg. imidazole and 1,2,4-triazole, pyridines, eg. 4-dimethylaminopyridine, and amides, eg. dimethylformamide, as well as mixtures of these compounds.
  • metal halides eg. sodium bromide and potassium iodide
  • azoles eg. imidazole and 1,2,4-triazole
  • pyridines eg. 4-dimethylaminopyridine
  • amides eg. dimethylformamide
  • the process for the preparation of the novel compounds is advantageously carried out by taking the starting material II, with or without one of the above diluents, and then adding the starting material III and an acid acceptor simultaneously or successively. It is however also possible to introduce the starting material III into one of the above diluents and then to add the starting material II and an acid acceptor, simultaneously or in optional sequence from two separate feeds.
  • the reaction is in many cases complete as soon as the components have been brought together; if not, the mixture is stirred for from 10 minutes to 10 hours at from -10° to 120° C., preferably from 0° to 100° C., especially from 20° to 80° C.
  • the compound I is isolated from the reaction mixture in a conventional manner, for example by distilling off the solvent or excess starting material II or III, or directly by filtration. In the latter case, the filter residue is washed with water or dilute alkali or acid to remove acidic or basic impurities, and is then dried. Where a water-immiscible diluent is used, it is also possible to extract the reaction mixture directly with water or dilute alkali or acid, and then to dry it and evaporate it down. It is however also possible to dissolve the residue in a water-immiscible solvent and wash the solution as described. The desired end products are thereby obtained in a pure form; if not, they can be purified further by recrystallization, chromatography or distillation.
  • the compounds II can be obtained by reacting the corresponding aniline derivative with a compound of the formula IV
  • Hal is halogen, for example chlorine or bromine.
  • the carboxylic acid derivatives of the formula III used as starting materials are known or can be prepared by known methods, cf. J. Amer. Chem. Soc. 77 (1955), 5359 and J. Chem. Soc. 1965, 5166.
  • the compounds I have an asymmetric carbon atom in the propionate side chain. They can be separated into the optical antipodes by conventional methods; the D-enantiomer has the more powerful microbicidal action.
  • optically active ester II can be prepared in a conventional manner, for example by reacting methylmercaptan or methanol or, preferably, their salts, especially their Na or K salts, with an acid halide of the optical antipode of the formula V.
  • the ester II is then reacted with III in accordance with the invention.
  • a suitable optically active organic base is, for example, ⁇ -phenylethylamine.
  • the product obtained is normally a mixture of two optical isomers or two atropic isomers or a mixture of these four possible isomers.
  • the fundamentally better fungicidal action of the enantiomeric D-form (as compared to the D,L-form or to the L-form) still applies and is not significantly influenced by the atropic isomerism.
  • the active ingredients according to the invention have a strong fungitoxic action. They cause no damage to crop plants in the concentrations necessary for combating fungi and bacteria. For these reasons they are suitable for use as crop protection agents for fighting fungi.
  • the new active ingredients exhibit a strong fungitoxic action on phytopathogenic fungi. They are suitable for combating for instance Erysiphe graminis in cereals, Erysiphe cichoriacearum in Cucurbitaceae, Erysiphe polygoni in beans, Podosphaera leucotricha and Phytophthora cactorum in apples, Phytophthora infestans in tomatoes and potatoes, Phytophthora parasitica in strawberries, Pseudoperonospora cubensis in cucumbers, Pseudoperonospora humuli in hops, Peronospora destructor in onions, Peronospora tabacina in tobacco, Peronospora sparsa in roses, Plasmopara viticola in grapes, Plasmopara halstedii in sunflowers, Sclerospora macrospora in Indian corn, Bremia lactucae in lettuce, Mucor mucedo in fruit
  • the application rates depend on the type of effect desired, and range from 0.1 to 5 kg of active ingredient per hectare.
  • Some of the active ingredients have curative properties, i.e., the agents may also be applied after the plants have been infected by the pathogen, and success is still ensured.
  • many of the new compounds have a systemic action, which means that visible plant parts may also be protected by a root treatment.
  • the new compounds may also be employed to control fungi which cause seedling and emergence diseases, e.g., Pythium and Aphanomyces species in Leguminosae and cotton.
  • the agents are applied as seed disinfectants at rates of from 10 to 200 g per 100 kg of seed.
  • the compounds are applied by spraying or dusting the plants with the active ingredients, or treating the seed with them.
  • the compounds may be applied before or after infection of the plants or seed by the fungi.
  • the active ingredients of the invention can be converted into the conventional formulations, e.g. solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the form of application depends entirely on the purpose for which the agent is to be used; at all events, it should ensure a fine and uniform distribution of the active ingredients, because fungicidal effectiveness is favorably influenced the finer the particles are.
  • the formulations are prepared in the conventional manner, for example by diluting the active ingredient with solvents and/or carriers, with or without the addition of emulsifiers and dispersants and, where water is used as the diluent, with or without an organic auxiliary solvent.
  • Suitable auxiliaries are, essentially, solvents, for example aromatics, e.g.
  • xylene and benzene chloroaromatics, e.g. chlorobenzene, paraffins, e.g. petroleum fractions, alcohols, e.g. methanol and butanol, amines, e.g. ethanolamine, and dimethylformamide and water; carriers, for example natural rock powders, e.g. kaolin, alumina, talc and chalk, and synthetic rock powders, e.g. highly disperse silica and silicates; emulsifiers, for example non-ionic and anionic emulsifiers, e.g. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates, and dispersants, for example lignin, sulfite waste liquors and methylcellulose.
  • chloroaromatics e.g. chlorobenzene
  • paraffins e.g. petroleum fractions
  • alcohols e.g. methanol and
  • the fungicidal agents generally contain from 0.1 to 95, preferably from 0.5 to 90, wt % of active ingredient.
  • the agents, and the ready-to-use formulations obtained therefrom e.g., solutions, emulsions, suspensions, powders, dusts, pastes or granules, are applied in the conventional manner, e.g. by spraying, atomizing, dusting, scattering, treating seed, or watering.
  • V. 20 Parts by weight of the compound of Example 4 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene- ⁇ -sulfonic acid, 17 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and triturated in a hammer mill.
  • a spray liquor is obtained containing 0.1% by weight of the active ingredient.
  • the above ready-to-use preparations may contain other active ingredients together with those according to the invention, e.g. herbicides, insecticides, growth regulators and other fungicides or may be mixed with fertilizers and applied together with these.
  • active ingredients e.g. herbicides, insecticides, growth regulators and other fungicides
  • fertilizers e.g. fertilizers, fertilizers and applied together with these.
  • the active ingredients are mixed with other fungicides, the fungicidal spectrum of action is in many cases broadened.
  • fungicides which can be combined with the compounds of the invention are: dithiocarbamates and their derivatives, e.g. iron(III) dimethyldithiocarbamate, zinc dimethyldithiocarbamate, manganese N,N-ethylene-bis-dithiocarbamate, manganese zinc, N,N-ethylenediamine-bis-dithiocarbamate, zinc N,N-ethylene-bis-dithiocarbamate, tetramethylthiuram disulfide, the ammonia complex of zinc N,N-ethylene-bis-dithiocarbamate and zinc, N,N'-propylene-bis-dithiocarbamate, and the ammonia complex of zinc N,N'-propylene-bis-dithiocarbamate and N,N'-polypropylene-bis-(thiocarbamoyl)-disulfide; nitro derivatives, e.g.
  • N-trichloromethylthiotetrahydrophthalimide N-trichloromethylthio-phthalimide, 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethyl phthalimidophosphonothioate, 5-amino-1-(bis-(dimethylamino)-phosphinyl)-3-phenyl-1,2,4-triazole, 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole, 2,3-dicyano-1,4-dithiaanthraquinone, 2-thio-1,3-dithio-(4,5-b)-quinoxaline, methyl 1-(butylcarbamoyl)-2-benzimidazole-carbamate, 2-methoxycarbonylamino-benzimidazole, 2-thiocyanatomethylthio-
  • dodecylguanidine acetate 3-(2-(3,5-dimethyl-2-hydroxycyclohexyl)-2-hydroxyethyl)-glutarimide, hexachlorobenzene, N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenyl-sulfuric acid diamide, 2,5-dimethyl-furan-3-carboxylic acid anilide, 2,5-dimethylfuran-3-carboxylic acid cyclohexylamide, 2-methyl-benzoic acid anilide, 2-iodo-benzoic acid anilide, 1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecyl-morpholine and its salts, 2,6-dimethyl-N-cyclodecyl-morpholine and its salts, diisopropyl 5-nitroisophthalate,
  • Leaves of tomato plants of the "Professor Rudloff” variety are sprayed with aqueous suspensions containing (dry basis) 80% (wt %) of active ingredient and 20% of sodium lignin sulfonate. 0.05 and 0.025% (dry basis) spray liquors are used. After the sprayed-on layer has dried, the leaves are infected with a zoospore suspension of Phytophthora infestans. The plants are then placed for 5 days in a steam-saturated (moist) chamber kept at 16° to 18° C. After this period, the disease has spread on the untreated control plants to such an extent that the fungicidal action of the compounds can be assessed.
  • aqueous suspensions containing (dry basis) 80% (wt %) of active ingredient and 20% of sodium lignin sulfonate. 0.05 and 0.025% (dry basis) spray liquors are used. After the sprayed-on layer has dried, the leaves are infected with a zoo
  • Leaves of potted vines of the Mueller-Thurgau variety are sprayed with aqueous emulsions containing (dry basis) 80% (by weight) of the active ingredient and 20% of emulsifier. 0.025% spray liquors (dry basis) are used.
  • the plants are placed, after the sprayed-on layer has dried, for 10 days in the greenhouse.
  • the leaves are then infected with a zoospore suspension of Plasmopara viticola.
  • the plants are then placed for 16 hours in a steam-saturated (moist) chamber at 24° C., and subsequently for 8 days in the greenhouse at 20° C. to 30° C.
  • To accelerate and intensify the sporangiophore discharge the plants are then again placed in the moist chamber for 16 hours. The extent of fungus spread is assessed on the undersides of the leaves.
  • Leaves of pot-grown wheat seedlings of the "Jubilar" variety are sprayed with aqueous emulsions consisting of 80% (by weight) of active ingredient and 20% of emulsifier, and dusted, after the sprayed-on layer has dried, with spores of wheat mildew (Erysiphe graminis var. tritici).
  • the plants are then placed in a greenhouse at 20° to 22° C. and 75 to 80% relative humidity. The extent of mildew spread is determined after 10 days.
  • Examples A, B, and C particularly the compounds of Examples 1 to 3 and 9 exhibited much more favorable properties than the prior art active ingredient furalaxyl (D,L-methyl-N-(2,6-dimethylphenyl)-N-fur-2-oyl alanate, German Laid-Open application DE-OS No. 2,513,732).

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  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
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US06/287,684 1980-08-14 1981-07-28 N-Disubstituted aniline derivatives, their preparation, their use as microbicides and agents for such use Expired - Fee Related US4410538A (en)

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DE3030736 1980-08-14
DE19803030736 DE3030736A1 (de) 1980-08-14 1980-08-14 N-disubstituierte anilinderivate, ihre herstellung, ihre verwendung als mikrobizide und mittel dafuer

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US (1) US4410538A (cs)
EP (1) EP0046497B1 (cs)
JP (1) JPS5767567A (cs)
AT (1) ATE10495T1 (cs)
AU (1) AU540667B2 (cs)
BR (1) BR8105186A (cs)
CA (1) CA1164000A (cs)
CS (1) CS224622B2 (cs)
DD (1) DD200142A5 (cs)
DE (2) DE3030736A1 (cs)
DK (1) DK359681A (cs)
GR (1) GR74601B (cs)
HU (1) HU185946B (cs)
IE (1) IE51494B1 (cs)
IL (1) IL63450A (cs)
MA (1) MA19252A1 (cs)
NZ (1) NZ198027A (cs)
PL (1) PL127385B2 (cs)
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Cited By (2)

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AU696611B2 (en) * 1995-03-31 1998-09-17 Nihon Nohyaku Co., Ltd. An agricultural and horticultural disease controller and a method for controlling the diseases
WO2012151500A1 (en) 2011-05-04 2012-11-08 Liquid X Printed Metals, Inc. Metal alloys from molecular inks

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DE3120804A1 (de) * 1981-05-25 1982-12-16 Basf Ag, 6700 Ludwigshafen N-substituierte 2-methylnaphthylamide, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von pilzen
DE3205639A1 (de) * 1982-02-17 1983-08-25 Hoechst Ag, 6230 Frankfurt Neue chloracetanilide, verfahren zu ihrer herstellung ihre verwendung als herbizide und sie enthaltende mittel
US6166054A (en) 1995-03-31 2000-12-26 Nihon Nohyaku Co., Ltd. Agricultural and horticultural disease controller and a method for controlling the diseases
JP2007045844A (ja) * 1995-03-31 2007-02-22 Nippon Nohyaku Co Ltd 農園芸用病害防除剤及びその使用方法
ID24100A (id) * 1997-10-31 2000-07-06 Nihon Nohyaku Co Ltd Turunan tiadiazol karboksamida, pengontrol penyakit tanaman dan penggunaannya

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DE2513732A1 (de) 1974-04-02 1975-10-16 Ciba Geigy Ag Mikrobizide und wachstumsregulierende mittel
DE2513788C3 (de) 1974-04-02 1978-02-09 Ciba-Geigy Ag, Basel (Schweiz) Substituierte Furan-2-carbonsäureanilide und Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende fungizide Mittel
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU696611B2 (en) * 1995-03-31 1998-09-17 Nihon Nohyaku Co., Ltd. An agricultural and horticultural disease controller and a method for controlling the diseases
WO2012151500A1 (en) 2011-05-04 2012-11-08 Liquid X Printed Metals, Inc. Metal alloys from molecular inks
US9487669B2 (en) 2011-05-04 2016-11-08 Liquid X Printed Metals, Inc. Metal alloys from molecular inks
US9920212B2 (en) 2011-05-04 2018-03-20 Liquid X Printed Metals, Inc. Metal alloys from molecular inks
US10738211B2 (en) 2011-05-04 2020-08-11 Liquid X Printed Metals, Inc. Metal alloys from molecular inks
US11118078B2 (en) 2011-05-04 2021-09-14 Liquid X Printed Metals, Inc. Metal alloys from molecular inks

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DE3167448D1 (en) 1985-01-10
IE51494B1 (en) 1987-01-07
AU540667B2 (en) 1984-11-29
IE811837L (en) 1982-02-14
IL63450A0 (en) 1981-10-30
DD200142A5 (de) 1983-03-23
DK359681A (da) 1982-02-15
NZ198027A (en) 1983-03-15
CA1164000A (en) 1984-03-20
ATE10495T1 (de) 1984-12-15
JPS5767567A (en) 1982-04-24
EP0046497A2 (de) 1982-03-03
PL127385B2 (en) 1983-10-31
DE3030736A1 (de) 1982-03-25
PL232598A2 (cs) 1982-04-26
MA19252A1 (fr) 1982-04-01
ZA815583B (en) 1982-08-25
IL63450A (en) 1984-11-30
EP0046497B1 (de) 1984-11-28
EP0046497A3 (en) 1982-03-17
AU7406281A (en) 1982-02-18
CS224622B2 (en) 1984-01-16
HU185946B (en) 1985-04-28
GR74601B (cs) 1984-06-29
BR8105186A (pt) 1982-04-27

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